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LITHIUM METHOXIDE: Chemical Properties, Uses, and Production

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Preparation

The process of preparing lithium methoxide involves adding 3 cm³ (3 mmol) of a 1.0 M solution in methanol to (11) (1.0 g, 2.8 mmol) in 15 cm³ of methanol while maintaining a nitrogen atmosphere at 0 °C. The mixture is stirred at room temperature for approximately 67 hours, after which 20 cm³ of water is incorporated, and the mix is extracted into dichloromethane (DCM). The resulting DCM solution is dried using magnesium sulfate and subsequently evaporated to yield a solid (1.1 g) that contains 4-methoxy-3,5-difluoro-2,6-dibromopyridine (22g) (19%), 2,6-dibromo-4,5-dimethoxy-3-fluoropyridine (22h) (5%), (23b) (39% in relation to an authentic sample), and (23a) (36%). Although column chromatography (with DCM and petrol at a 7:3 ratio) and preparative scale GLC (10% SE30 at 140 °C) did not sufficiently separate the products, carbon NMR spectra and GCMS of a mixed sample (22g) and (23b) were successfully obtained, with carbon spectra assignment verified by comparison with (23b).

Chemical Properties

Lithium Methoxide [865-34-9], with a molecular formula of LiOCH3 and a molecular weight of 37.98, appears as a white solid. It is soluble in methanol but has minimal solubility in aprotic organic solvents. Available commercially as a 99% fine crystalline solid and a 10% solution in methanol, it is frequently employed as a base and particularly as a catalyst for transesterification reactions.

Uses

This compound is utilized in the sol-gel synthesis of lithium borophosphates, as well as in various deprotonation reactions within organic synthesis. Its mild basic nature makes it particularly valuable for transesterification processes.

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Purification Methods

The most likely contaminant in lithium methoxide is lithium hydroxide (LiOH), which can result from hydrolysis due to moisture exposure. It is critical to keep the material dry; it can be dehydrated under a vacuum at temperatures ranging from 60-80°C in a dry nitrogen atmosphere using an oil pump for several hours. Always store the product under nitrogen in colder conditions. The IR spectrum should not display any bands above cm-1, as documented in scientific literature [Suebold J Org Chem 21, Beilstein 1 IV, .].

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Methanol - The Safe, Clean, and Versatile Energy Source of the Future

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